Synthesis of 9-Phenylacridines via Ortho-Lithiation-Cyclization Sequence

Khimiya Geterotsiklicheskikh Soedinenii 2014
Artis Kinēns, Toms Kalniņš, Edgars Sūna

Herein, we describe a previously unreported formation of acridines from triarylcarbinols under acidic conditions. Thus, treatment of tertiary alcs. with conc. aq. HCl in glacial AcOH at 90° provided 9-phenylacridines in 91-92% yield. The starting tertiary alcs. were prepd. by double addn. of ortho-lithiated pivaloyl anilines to benzoyl chloride in 76 and 68% yield, resp. Overall, the two-step ortho-lithiation cyclization sequence constitutes a convenient approach to 9-phenylacridines.

Keywords
acridine oxazine tertiary alcohol cyclization ortho-lithiation

Kinēns, A., Kalniņš, T., Sūna, E. Synthesis of 9-Phenylacridines via Ortho-Lithiation-Cyclization Sequence. Khimiya Geterotsiklicheskikh Soedinenii, 2014, Vol.50, Iss.10, pp.1629-1633. ISSN 0132-6244.

Publication language
English (en)